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The reactions of 6-(Hydroxymethyl)-2,2-dimethyl-1-azaspiro[4.4]nonanes with methanesulfonyl chloride or pph3-cbr4. / Khoroshunova, Yulia V.; Morozov, Denis A.; Taratayko, Andrey I. et al.

In: Molecules, Vol. 26, No. 19, 6000, 01.10.2021.

Research output: Contribution to journal › Article › peer-review

Harvard

Khoroshunova, YV, Morozov, DA, Taratayko, AI, Dobrynin, SA, Eltsov, IV, Rybalova, TV, Sotnikova, YS, Polovyanenko, DN, Asanbaeva, NB & Kirilyuk, IA 2021, 'The reactions of 6-(Hydroxymethyl)-2,2-dimethyl-1-azaspiro[4.4]nonanes with methanesulfonyl chloride or pph3-cbr4', Molecules, vol. 26, no. 19, 6000. https://doi.org/10.3390/molecules26196000

APA

Khoroshunova, Y. V., Morozov, D. A., Taratayko, A. I., Dobrynin, S. A., Eltsov, I. V., Rybalova, T. V., Sotnikova, Y. S., Polovyanenko, D. N., Asanbaeva, N. B., & Kirilyuk, I. A. (2021). The reactions of 6-(Hydroxymethyl)-2,2-dimethyl-1-azaspiro[4.4]nonanes with methanesulfonyl chloride or pph3-cbr4. Molecules, 26(19), [6000]. https://doi.org/10.3390/molecules26196000

Vancouver

Khoroshunova YV, Morozov DA, Taratayko AI, Dobrynin SA, Eltsov IV, Rybalova TV et al. The reactions of 6-(Hydroxymethyl)-2,2-dimethyl-1-azaspiro[4.4]nonanes with methanesulfonyl chloride or pph3-cbr4. Molecules. 2021 Oct 1;26(19):6000. doi: 10.3390/molecules26196000

Author

Khoroshunova, Yulia V. ; Morozov, Denis A. ; Taratayko, Andrey I. et al. / The reactions of 6-(Hydroxymethyl)-2,2-dimethyl-1-azaspiro[4.4]nonanes with methanesulfonyl chloride or pph3-cbr4. In: Molecules. 2021 ; Vol. 26, No. 19.

BibTeX

@article{4b8fdac4c3164b1f823f08c560db2a66,
title = "The reactions of 6-(Hydroxymethyl)-2,2-dimethyl-1-azaspiro[4.4]nonanes with methanesulfonyl chloride or pph3-cbr4",
abstract = "Activation of a hydroxyl group towards nucleophilic substitution via reaction with me-thanesulfonyl chloride or PPh3-CBr4 system is a commonly used pathway to various functional derivatives. The reactions of (5R(S),6R(S))-1-X-6-(hydroxymethyl)-2,2-dimethyl-1-azaspiro[4.4]nonanes 1a–d (Х = O·; H; OBn, OBz) with MsCl/NR3 or PPh3-CBr4 were studied. Depending on substituent X, the reaction afforded hexahy-dro-1H,6H-cyclopenta[c]pyrrolo[1,2-b]isoxazole (2) (for X = O), a mixture of 2 and octahydrocy-clopenta[c]azepines (4–6) (for X = OBn, OBz), or perhydro-cyclopenta[2,3]azeto[1,2-a]pyrrol (3) (for X = H) derivatives. Alkylation of the latter with MeI with subsequent Hofmann elimination afforded 2,3,3-trimethyl-1,2,3,4,5,7,8,8a-octahydrocyclopenta[c]azepine with 56% yield.",
keywords = "Alkylation, Appel reaction, Azepane, Hofmann elimination, Nitroxide",
author = "Khoroshunova, {Yulia V.} and Morozov, {Denis A.} and Taratayko, {Andrey I.} and Dobrynin, {Sergey A.} and Eltsov, {Ilia V.} and Rybalova, {Tatyana V.} and Sotnikova, {Yulia S.} and Polovyanenko, {Dmitriy N.} and Asanbaeva, {Nargiz B.} and Kirilyuk, {Igor A.}",
note = "Funding Information: Funding: This work was funded by RFBR 18-53-76003-ERA-A (ERA.Net RUS+ project ST2017-382: NanoHyperRadicals). Publisher Copyright: {\textcopyright} 2021 by the authors. Licensee MDPI, Basel, Switzerland.",
year = "2021",
month = oct,
day = "1",
doi = "10.3390/molecules26196000",
language = "English",
volume = "26",
journal = "Molecules",
issn = "1420-3049",
publisher = "Multidisciplinary Digital Publishing Institute (MDPI)",
number = "19",

}

RIS

TY - JOUR

T1 - The reactions of 6-(Hydroxymethyl)-2,2-dimethyl-1-azaspiro[4.4]nonanes with methanesulfonyl chloride or pph3-cbr4

AU - Khoroshunova, Yulia V.

AU - Morozov, Denis A.

AU - Taratayko, Andrey I.

AU - Dobrynin, Sergey A.

AU - Eltsov, Ilia V.

AU - Rybalova, Tatyana V.

AU - Sotnikova, Yulia S.

AU - Polovyanenko, Dmitriy N.

AU - Asanbaeva, Nargiz B.

AU - Kirilyuk, Igor A.

N1 - Funding Information: Funding: This work was funded by RFBR 18-53-76003-ERA-A (ERA.Net RUS+ project ST2017-382: NanoHyperRadicals). Publisher Copyright: © 2021 by the authors. Licensee MDPI, Basel, Switzerland.

PY - 2021/10/1

Y1 - 2021/10/1

N2 - Activation of a hydroxyl group towards nucleophilic substitution via reaction with me-thanesulfonyl chloride or PPh3-CBr4 system is a commonly used pathway to various functional derivatives. The reactions of (5R(S),6R(S))-1-X-6-(hydroxymethyl)-2,2-dimethyl-1-azaspiro[4.4]nonanes 1a–d (Х = O·; H; OBn, OBz) with MsCl/NR3 or PPh3-CBr4 were studied. Depending on substituent X, the reaction afforded hexahy-dro-1H,6H-cyclopenta[c]pyrrolo[1,2-b]isoxazole (2) (for X = O), a mixture of 2 and octahydrocy-clopenta[c]azepines (4–6) (for X = OBn, OBz), or perhydro-cyclopenta[2,3]azeto[1,2-a]pyrrol (3) (for X = H) derivatives. Alkylation of the latter with MeI with subsequent Hofmann elimination afforded 2,3,3-trimethyl-1,2,3,4,5,7,8,8a-octahydrocyclopenta[c]azepine with 56% yield.

AB - Activation of a hydroxyl group towards nucleophilic substitution via reaction with me-thanesulfonyl chloride or PPh3-CBr4 system is a commonly used pathway to various functional derivatives. The reactions of (5R(S),6R(S))-1-X-6-(hydroxymethyl)-2,2-dimethyl-1-azaspiro[4.4]nonanes 1a–d (Х = O·; H; OBn, OBz) with MsCl/NR3 or PPh3-CBr4 were studied. Depending on substituent X, the reaction afforded hexahy-dro-1H,6H-cyclopenta[c]pyrrolo[1,2-b]isoxazole (2) (for X = O), a mixture of 2 and octahydrocy-clopenta[c]azepines (4–6) (for X = OBn, OBz), or perhydro-cyclopenta[2,3]azeto[1,2-a]pyrrol (3) (for X = H) derivatives. Alkylation of the latter with MeI with subsequent Hofmann elimination afforded 2,3,3-trimethyl-1,2,3,4,5,7,8,8a-octahydrocyclopenta[c]azepine with 56% yield.

KW - Alkylation

KW - Appel reaction

KW - Azepane

KW - Hofmann elimination

KW - Nitroxide

UR - http://www.scopus.com/inward/record.url?scp=85116594968&partnerID=8YFLogxK

U2 - 10.3390/molecules26196000

DO - 10.3390/molecules26196000

M3 - Article

C2 - 34641544

AN - SCOPUS:85116594968

VL - 26

JO - Molecules

JF - Molecules

SN - 1420-3049

IS - 19

M1 - 6000

ER -

ID: 34400601